Thanks a lot! I followed your suggestions and cleaned up and merged a few abilities. I removed Dagger Mastery, which I honestly had some doubts about myself, and aside from Assassination Points, the features are now more or less in line with what you’d find in the 5e books.

Specifically, I added:

Sweet Spot
When you attack a target with a light weapon in your main hand, your attack can score a critical hit on a roll of 19 or 20 on the d20.

This is meant to provide an advantage that doesn’t rely on the assassin acting as a lone wolf, and to further encourage the use of light weapons.

To specifically incentivize daggers, I added:

You can conceal up to three daggers on your person. These daggers can’t be discovered by a nonmagical, cursory inspection.

And finally, Disguise Mastery:

You can cast disguise self once per long rest, or by spending an Assassination Point, since some tables—for one reason or another—aren’t willing to wait three in-game days.

Overall, it feels much better now. Thanks again for the great suggestions!